2,6-dichloro-3,5-dicyano-4-aryl pyridines



United States Patent 3,468,895 2,6-DICHLORO-3,5-DICYANO-4-ARYL PYRIDINESGiinther Mohr, Darmstadt, Konrad Niethammer, Traisa, and Sigmund Lustand Gerhart Schneider, Darmstadt, Germany, assignor to E. MerckAktiengesellschaft, Darmstadt, Germany No Drawing. Original applicationMar. 30, 1964, Ser. No. 355,929, now Patent No. 3,284,293, dated Nov. 8,1966. Divided and this application July 27, 1966, Ser. No. 568,137Claims priority, application Germany, Apr. 2, 1963, M 56,343 Int. Cl.C07d 31/46; AOln 9/22 US. Cl. 260-2943 8 Claims ABSTRACT OF THEDISCLOSURE Compounds of the following formula exhibit fungicidalactivity:

NC CN wherein R is selected from the group consisting of phenyl,naphthyl, pyridyl, substituted phenyl where the substituted moiety is atleast one member of the group consisting of CH C H CH O, C H O, OCH O,HO, F, Cl, Br, N0 NH and dialkyl amino containing 1-6 carbon atoms peralkyl group.

This is a divisional application of parent application Ser. No. 355,929,filed Mar. 30, 1964, and claims priority through said parent applicationof German patent application, Ser. No. M 56,343, filed Apr. 2, 1963, nowPatent No. 3,284,293.

This invention relates to novel fungicides having a wide range ofactivity.

It has been found that 4-substituted 2,6-dichloro-3,5- dicyano-pyridinesof the formula J:CN

wherein: R is any one of alkyl containing 1-8 carbon atoms, phenyl,naphthyl or pyridyl group, said aromatic compounds being optionallysubstituted in one or more places CH3, C2H5, CH30, C H O, H0, F, Cl, Br,N0 NH or dialkylarnino (alkyl u to C have a pronounced fungicidalaction. The 2,6-dichlor0-3,5- dicyano-4-phenyl-pyridine (I) isespecially effective.

The fungicidal activities of these compounds are characterizedespecially by their wide range, besides being very effective againstthose fungi which can also be fought with the usual fungicidal agents ofaverage range, these new agents also have a definite inhibiting eifecton the powdery mildew. The mildew fungi have heretofore been foughtsuccessfully only with sulfur preparations or with the specific mildewfungicide 2,4-dinitro-6-sec.-octylphenylcrotonate, although the latteris practically inefiective against other fungi.

The compounds of this invention are characterized by only slighttoxicity For example, the LD of I for oral application to rate is above5 g./ kg.

Patented Sept. 23, 1969 (a) Prior art compounds:

A Zinc-dimethyl-dithiocarbamate B Tetramethyl-thiuram-disulfide CN-trichloromethylthio-tetrahydro-phthalimide D2,4-dinitro-6-sec.-octylphenyl-crotonate EZinc-ethylene-bis-(dithiocarbamate) F N-trichloromethylthio-phthalimide(b) Compounds of this invention:

I 2,6-dichloro-3,5 dicyano-4-phenyl-pyridine II2,6-dichl0ro-3,5-dicyano-4-rnethyl-pyridine III2,6-dichloro-3,S-dicyano-4-isopropyl-pyridine IV2,6-dichloro-3,5-dicyano-4-(p-nitrophenyl)- pyridine V2,6-dichloro-3,5-dicyano-4-(m-nitrophenyl)- pyridine VI2,6-dichloro-3,5-dicyano-4-ethyl-pyridine VII2,6-dichloro-3,5dicyano-4-propyl-pyridine (I) SPORE GERMINATION TESTSThe action in vitro upon conidicspores of Venturia inaequalis (applescab), Alternaria spec. (leaf spot fungus), Cladosporium fulvum (brownand stain spots on tomatoes), and Barrytis cinerea (brown fungus rot)was tested by the known spore germination testing process. The resultsof these tests are given in the following Tables 1 to 4. The amount ofthe active agent is that which is necessary to prevent 50 to of thespores from germinating (DL to DL s average value from 3 tests).

TABLE 1.SLIDES, SPORE GERMINATION TEST Test fungus: Ventun'a inaequalisIn mgJlOO em.

Active Agent DL D11 I 0. 010 0. 022 II 0. 010 0. 017 III 0. 010 0. 020IV 0. 0019 0. 0038 V -1 0. 0026 0. 0065 TABLE 2.SLIDES, SPOREGERMINATION TEST Test fungus: Alternaria spec.

In mg./ em.

Active Agent DL 50 DL 95 TABLE 3.SLIDES, SPORE GEMINATION TEST Testfungus: Cladosporium fulvum In mg./100 cm.

(II) ACCELERATED SIMULATED FIELD TESTS FOR ORIENTATION The excellentfungicidal action in vitro of compound I was confirmed in someexperiments on hosts infected with important pathogenic fungi and wascompared with known fungicidal agents.

(1) Prevention of infection with Plasmopara viticola in vine leavesMethod.-The active agents were suspended in water with the help of 1part by weight of polyoxy-ethylenesorbitan-mono-oleate. Isolated vineleaves of the silvaner variety were sprayed on their under sides withthis suspension. After the suspension had dried, drops of a sporesuspension of the tested fungus were deposited on the intercostal areasof the leaf surface. After 24 hours the drops were removed by suction.The leaves were then stored in a damp chamber at room temperature underillumination until used.

Each recorded value is an average of three separate tests and representsthe percentage of inoculated places where infection was prevented by thesprayed coating.

(x) Denotes phytotoxic, the attack being impossible to judge perfectly.

(2) Spraying of tomatoes against infection by Phytophthora infestansMethod.Tomato plants (Lukullus) are sprayed in their 3-sequence leafstage with polyoxyethylene-sorbitan-mono-oleate in a 1:1 watersuspension. After the suspension has dried the leaves are sprayed with azoospore supsension of Phytophthora infestans and allowed to stand 24hours at 12 to 50 C. in a 100% moisture saturated atmosphere.

The table gives the infection results in percent infected.

TABLE 6 Test fungus: Phytophthora infealane Concentrations of activeagent in suspension Active agent Percent infected, control=100 (3)Spraying of wheat plants against Erysiphe graminis forrna specialistritici Method.-Wheat seed-plants were infected with conidia of erysiphe and were kept in a greenhouse at 20 to 25 C. 2, 4, and 6 days afterthe infection some of the experimental plants were sprayed with asuspension of the active agent in water(polyethylene-sorbitan-monooleate, 1:1). They were evaluated 10 and 14days after infection. Infection of the leaves and of the coleoptiles wasrecorded separately.

TABLE 7 Test fungus: Erysiphe graminie f. sp. triticz' Percent infectionreduction in concentration range 0.20.02%

Areas of 5 n1 each, covered with vines of the Riesling, Silvaner andMiiller-Thurgau varieties were sprayed 9 times in 9 weeks withsuspensions of the active agents. One week after the last spraying theleaves were evaluated. Those which had more than three infected placeswere considered as being infected, and their percentage of the totalnumber of leaves was recorded.

TABLE 8 Concentration, percent Infected Kind of vine percent RieslingActive Agent Silvaner Untreated The results show that agent I of thisinvention is more effective than agents E and F with which it wascompared.

5 iv PLANT TOLERANCE (1) Drop-application test on the primary leaves ofbeans Method.The upper sides of the primary leaves of almost completelydeveloped bush beans (potted Saxa plants) were wetted with an aqueoussuspension of the fungicidal agent (2 drops per leaf). The agent wasused with polyoxyethylene sorbitan-mono-oleate 1: 1. Then the leaf waspunctured from below into the drop with a needle.

TABLE 9.PHYTOTOXICITY OF FUNGICIDAL AGENTS TOWARD LEAF TISSUES OF BEANPLANTS [Formation of dark zones around the punctured places one Weekafter treatment; diameter in mm. (average of four places) for variousconcentrations] Concentration of active ingredient, percent Active agent5. 2. 0 1. 0 0. 5 0. 2

Control (Water drop)--. 0 0 0 0 0 (2) Plant spraying Young plants ofoats, wheat, pumpkin, bush beans and tomatoes, as well as vine cuttingsand apples were sprayed with an aqueouspolyoxyethylene-sorbitan-mono-oleate suspension of the fungicidal agent(1:1) until they were dripping Wet. The tolerance for I Was generallyvery good, even in the highest concentration of 0.4 to 0.5%, especiallyin comparison with agent D.

In addition to their wide range of applicability and their effectivenessfor preventing mildew infection, the new compounds are alsocharacterized by good plane compatibility.

The 4 substituted 2,6 dichloro-3,S-dicyano-pyridines can be producedfrom the corresponding 4-substituted 3,5-dicyano-6-hydroxy-Z-pyridonesby reaction with a chlorinating agent without or with the addition of asolvent. As a starting material, consideraiton can be given e.g., to4-phenyl-,4-o-, 4-mor 4 p-tolyl-, 4-o-, 4mor 4-p-methoxyphenyl-, 4-o-,4-m, or 4-phydroxyphenyl-, 4-a-naphthyl-, 4-5-naphthyl-, 4 0-, 4-m or 4p-halogenphenyl-, 4-o-, 4-mor 4-p-nitro-phenyl-, 4-o-, 4-mor 4-p-aminoor-dialkylaminophenyl-3,5-dicyano-6-hydroxy-Z-pyridone. Suitablechlorinating agents are e.g. phosphorus pentachloride, phosphorusoxychloride, phosphorus trichloride, thionyl chloride, sulfuryl chlorideor mixtures thereof with or without the addition of solvents. Suitablesolvents are inert organic liquids such as benzene, chlorinated benzene,dimethyl-formamide, tertiary bases such as pyridine, quinoline,triethylamine, tributylamine, dimethylaniline or mixtures of those aloneor with other inert solvents.

The reaction will occur at room temperature, but it is advantageous towarm or boil the mixture for a while. The reaction is generallycompleted after 0.5 to 10 hours, depending on the conditions.

2,6-dichloro-3,5-dicyano-4-methyl-pyridine and the corresponding4-ethyl-compound are known, (collection of Czechoslovak chemicalcommunications, 25, 2173 (1960)), but not their prominent fungicidalactivity.

The 4-aryl-3,S-dicyano-6-hydroxy-2-pyridones are in part known (seeJour. Chem. Soc., vol. 117, (1920), p 1473). They can be produced bycondensation of 2 molecules cyanacetamide with suitable aromaticaldehydes in the presence of a basic condensation agent. Thecyanacetamide can be prepared from cyanoacetic ester and ammonia, or canbe produced in situ from chloroacetic ester, potassium or sodium cyanideand ammonia. Suitable condensation agents are e.g. ammonia, sodium orpotassium hydroxide or sodium or potassium alcoholates. Suitablealdehydes are acetaldehyde, propionaldehyde, butyraldehyde,isobutyraldehyde, 3-methylbutane-aldehyde, benzaldehyde, o-, mandp-tolylaldehyde, o-, mand p-methoxybenzaldehyde, o-, mandp-hydroxybenzaldehyde, o-, mand p-chlorobenzaldehyde, o-, m andpbromobenzaldehyde, o-, mand p-nitrobenzaldehyde, o-, mand p-arninoor-dialkylaminobenzaldehyde wherein alkyl C l-naphthaldehyde,2-naphthaladehyde and 2-, 3- and 4-pyridine-aldehyde.

Particularly suitable fungicidal agents according to this invention are2,6-dichloro-3,5-dicyano-4-methy1-, -4-ethyl-, -4-propyl-,-4-isopropyl-, -4-butyl-, -4 isobutyl-, -4-amyl-, -4-isoamyl, -4-hexyl,-4-heptyl-, -4-octyl-, -4-phenyl-, -4-o-tolyl-, -4-m-tolyl-,-4-p-tolyl-, -4-(o-ethylphenyl)-, -4-(m-ethylphenyl),-4-(p-cthylphenyl-, -4-(o-methoxyphenyl) -4-(m-methoxyphenyl)-4-(p-methoxyphenyl) -4-(,4-dimethoxyphenyl)-, -4-(p-ethoxyphenyl),-4-(3,4- methylendioxyphenyl)-, -4-(o-hydroxyphenyl)-,-4-(mhydroxyphenyl)-, -4-(p-hydroxyphenyl)-, -4-(2,4-dihydroxyphenyl)-,-4-(o fiuorophenyl)-, 4 (m fluorophenyl)-, -4-(p-fluorophenyl)-,-4-(o-chlorophenyl)-, -4- (m chlorophenyl)-, -4-(p chlorophenyl)-,-4-(2,4 dichlorophenyl)-, -4-(o bromophenyl)-, -4-(m bromophenyl)-,-4(p-bromophenyl)-, -4-(2,4-dibromophenyl)-, -4-(o-nitrophenyl)-, -4-(mnitrophenyl)-, -4-(p nitropheny1)-, -4-(o-aminophenyl)-,-4-(m-aminophenyl)-, -4- (p-aminophenyl)-, -4-(o-dimethylaminophenyl)-,-4-(mdimethylaminophenyl)-, -4-(p dimethylaminophenyl)-, -4-(pdiethylaminophenyl)-, -4-(p di n hexylaminophenyl)-, -4-(l-naphthyl)-,-4-(2-naphthyl)-, -4-(2-pyridyl)-, -4-(3-pyridyl)- and-4-(4-pyridyl)-pyridine.

The fungicidal compounds of this invention can be incorporated in theforms generally used. By the addition of the usual carrier and/or fillersubstances it is possible to produce spraying or dusting materials whichcan be mixed with other substances such as dispersing or wetting agents.It is also possible to prepare solution or emulsions therefrom which canbe applied e.g. by atomization after the addition of suitable agents.Suitable solvents for this purpose are especially certain hydrocarbonssuch as gasoline, petroleum, benzene, toluene, xylene, tetralin,decalin, or mixtures thereof. It is also possible to use the fungicidalagents of this invention in mixtures with other fungicidal agents. Thepreparations generally contain from 1 to of the active agent.

Other fungicidal agents to be used in mixtures with the compounds ofthis invention are for instance:

N-trichloromethylthio-tetrahydro-phthalimide2,3-dicyano-1,4-dithiaanthraquinone n-dodecylguanidine acetatedipyrrolidyl-thiuram-disulfide triphenyltin-acetate ferricN,N-dimethyl-dithio-carbamate 2,4-dinitro-6-sec. octylphenyl-crotonatemanganese-ethylene-bis-dithio-carbamate pentachloro-nitrobenzene2,3,5,6-tetrachloro-nitrobenzene tetramethyl-thiuram-disulfidezinc-ethylene-bis-(dithiocarbamate) zinc-N,N-dimethyl-dithiocarbamate2-heptadecyl-Z-imidazoline acetate griseofulvinN-trichloromethylthio-phthalimide furthermore salts and organometalliccompounds of mercury, copper, and arsenic such as phenylmercuric acetateor basic cupric chloride as well as the usual sulfur fungicides such asbarium sulfide.

The preparations may generally contain 1 to 95% of the known fungicidein addition to the fungicide according to the invention.

Without further elaboration, it is believed that one skilled in the artcan, using the preceding description, utilize the present invention toits fullest extent. The following preferred specific embodiments are,therefore, to be construed as merely illustrative, and not limitative ofthe remainder of the specification and claims in any way whatsoever.

EXAMPLE 1 23.7 g. dry 3,5-dicyano-6-hydroxy-4-phenyl-2-pyridone(produced according to Journal of the Chemical Society (London) vol. 117(1920), p. 1473) or 25.5 g. of its ammonium salt in 150 ml.chlorobenzene are reacted with 41.7 g. phosphorus pentachloride andboiled two hours. The dark red reaction mixture is poured over ice, theorganic phase separated, washed to neutrality with sodium 'bicarbonatesolution, dried over sodium sulfate and concentrated. The yield is 12.0g. (44% of the theoretical) 2,6-dichloro-3,5-dicyano-4-phenyl pyridine(I) melting at 192196 C. After recrystallization from benzene orethanol, colorless crystals melting at 203204 C. are obtained.

EXAMPLE 2 20 g. 3,5 dicyano 6 hydroxy 4 phenyl 2 pyridone or 21.5 g. ofits ammonium salt and 6 ml. pyridine in 150 ml. dry benzene are heatedover night under reflux with 20 ml. phosphorus oxychloride and are thenpoured into 200 ml. benzene and 300 ml. ice water. The benzene phase iswashed with water and sodium bicarbonate solution, dried over sodiumsulfate, and evaporated to dryness. The yield is 14.5 g. (63%theoretical of I. M.P. 202- 204" C.

EXAMPLE 3 20 g. 3,5 dicyano 6 hydroxy 4 p tolyl pyridone (producedaccording to Le.) or 21.5 g. of its ammonium salt are mixed with 80 g.phosphorus pentachloride and heated one hour to 130-140 C. Aftercooling, the mixture is poured into ice water and the precipitaterecrystallized several times from ethanol or benzene. The 2,6-dichloro-3,S-dicyano-4-p-tolyl-pyridine thus obtained melts at 240-242C. Yield 90%.

By analogy the following compounds can be obtained:

2,6-dichloro-3,5-dicyano-4- (p-chlorophenyl)-pyridine,

F. 282284 2,6-dichloro-3,5-dicyano-4-(m-nitrophenyl)-pyridine,

F. 214216 2,6-dichloro-3 ,5 dicyano-4- p-nitrophenyl) -pyridine,

P. 206-207" 2,6-dichloro-3 ,5 -dicyano-4- 3-pyridy1) -pyridine,

F. 183l85 2,6-dichloro-3,5-dicyano-4-(4-pyridyl)-pyridine,

F. 196-198" 2,6-dichloro-3,5-dicyano-4-propyl-pyridine, F, 104-1062,6-dichloro-3,S-dicyano-4-isopropyl-pyridine,

F. 120-122 2,6-dich1oro-3,5-dicyano-4-disobutyl-pyridine,

EXAMPLE 4 By analogy to Example 3, from the corresponding 4- substituted3,S-dicyano-6-hydroxy-2-pyridones or their ammonium salts, the followingcompounds can be obtained.

2,6-dichloro-3,5-dicyano-4-butyl-pyridine2,6-dichloro-3,5-dicyano-4amyl-pyridine2,6-dichloro-3,S-dicyano-4-isoamyl-pyridine2,6-dichloro-3,S-dicyano-4-hexyl-pyridine2,6-dichloro-3,S-dicyano-4-heptyl-pyridine2,6-dichloro-3,5-dicyano-4-octyl-pyridine2,6-dichloro-3,5-dicyano-4-(o-tolyl)-pyridine2,6-dichloro-3,5-dicyano-4- (m-tolyl)-pyridine2,6-dichloro-3,5-dicyano-4-(o-ethylphenyl)-pyridine2,6-dichloro-3,5-dicyano-4-(p-ethylphenyl)-pyridine2,6-dichloro-3,5-dicyano-4-(o-methoxyphenyl)-pyridine 2,6-dichloro-3 ,5-dicyano-4- (m-methoxyphenyl) -pyridine2,6-dichloro-3,5-dicyano-4-(p-methoxyphenyD-pyridine2,6-dichloro-3,5-diCyan-4 (3,4-dimethoxyphenyl) pyridine 82,6-dichloro-3,5-dicyano-4- (p-ethoxyphenyl) -pyridine2,6-dichloro-3,5-dicyano-4- 3,4-methylendioxyphenyl) pyridine2,6-dichloro-3,5-dicyano-4- (o-hydroxyphenyl -pyridine2,6-dichloro-3,5-dicyano-4- (m-hydroxyphenyl -pyridine2,6-dichloro-3,5-dicyano-4- (p-hydroxyphenyl) -pyridine2,6-dichloro-3,5-dicyano-4- (2,4-dihydroxyphenyl) pyridine2,6-dichloro-3 ,5-dicyano-4- (4-hydroxy-3-methoxyphenyl) pyridine2,6-dichloro-3,5-dicyano-4- (o-fluorophenyl -pyridine2,6-dichloro-3,5dicyano-4-(m-fluorophenyl)-py1idine2,6-dichloro-3,5-dicyano-4- (p-fiuorophenyl) -pyridine2,6-dichloro-3,5-dicyano-4- o-chlorophenyl -pyridine2,6-dichloro-3,5-dicyauo-4- (m-chlorophenyl -pyridine2,6-dichloro-3,5-dicyano-4- (2,4-dichlorophenyl -pyridine2,6-dichloro-3,5-dicyano-4- (o-bromophenyl -pyridine 2,6-dichloro-3 ,5-dicyano-4- m-bromophenyl) -pyridine 2,6-dichloro-3 ,5 -dicyano-4-p-bromophenyl -pyridine 2,6-dichloro-3,5-dicyano-4- (2,4-dibromophenyl)-pyridine 2,6-dichloro-3 ,5-dicyano-4- (o-nitrophenyl) -pyridiue2,6-dichloro-3,5-dicyano-4- (o-aminophenyl -pyridine2,6-dichloro-3,5-dicyano-4- (m-aminophenyl) -pyridine 2,6-dichloro-3,5-dicyano-4- (p-aminophenyl) -pyridine 2 5 2,6-dichloro-3,5-dicyano-4-(o-dimethylaminophenyl) pyridine 2,6-dichloro-3,5-dicyano-4-m-dimethylaminophenyl) pyridine 2,6-dichloro-3,5-dicyano-4-(p-dimethylaminophenyl) pyridine 2,6-dichloro-3,5-dicyano-4-(p-diethylaminophenyl) pyridine 7 2,6-dichloro-3,5-dicyano-4-(p-di-n-hexylaminophenyl) pyridine 5 2,6-dichloro-3,5-dicyano-4-(1-naphthyl)-pyridine 2,6-dichloro-3,5-dicyano-4- Z-naphthyl -pyridine 2,6-dichloro-3,5 -dicyano-4- (2-pyridyl) -pyridine.

The following examples are preparations suitable toSodium-isobutyl-naphthaline sulfonate (technical) Bolus or chalkfungicidal purposes. Instead of the specific active agent 0 are groundintimately together. The resulting powder can be sprayed or atomized asa dilute aqueous suspension.

EXAMPLE '6 A wettable powder:

Percent 2,6-dichloro-3,5-dicyano-4-methyl-pyridine B0Oleic-acid-N-methyl-tauride 5 Fullers earth 15 are ground to thenecessary fineness. By dilution with water a finely divided emulsion isobtained which is suitable for spraying or atomizing.

EXAMPLE 7 A dusting material:

Percent 2,6-dichloro-3,5-dieyano-4-(p-nitrophenyl)-pyridine Talcum areintimately ground and applied with a suitable duster.

EXAMPLE 8 A spraying solution:

A solution of 3% 2,6-dichloro-3,5-dicyano-4-(3 manner through a nozzle.

pyridyl)-pyridine in chloroform is atomized in the usual 9 EXAMPLE 9 Anemulsion concentrate:

Percent 2,6-dichloro-3,S-dicyano-4-octyl-pyridine 10 Dimethyl-formamide45 Xylene Fatty acid-polyglycol-ester 30 are mixed. The resultingsolution is emulsified in water and is sprayed or atomized.

EXAMPLE 10 A wettable or dust powder:

are ground to the required fineness. The powder thus obtained can besprayed in the form of dilute aqueous suspensions or applied with asuitable duster.

EXAMPLE 11 A wettable powder:

Percent N-trichloromethylthiotetrahydrophthalimide2,6-dichloro-3,5-dicyano-4-phenyl-pyridine 30 Bentonite 4O Sulfiteliquor powder 7 Sodium salt of the condensation product from oleic acidand methyltaurine (technical grade 32%) 3 are ground intimately. Theresulting powder can be sprayed or atomized as a dilute aqueoussuspension.

EXAMPLE 12 A wettable powder:

Percent Zinc-ethylene-bis-(dithiocarbamate) 402,6-dichloro-3,S-dicyano-4-phenyl-pyridine 10 Bolus 40 Sulfite liquorpowder 8 Isobutyl naphthalene sulfonates 2 are ground intimately. Theresulting powder can be sprayed or atomized as a dilute aqueoussuspension.

From the foregoing description, one skilled in the art can easilyascertain the essential characteristics of this invention, and withoutdeparting from the spirit and scope thereof, can make various changesand modifications of the invention to adapt it to various usages andconditions. Consequently, such changes and modifications are properly,equitably, and intended to be, within the full range of equivalence ofthe following claims.

What is claimed is:

1. A compound of the formula:

wherein R is selected from the group consisting of phenyl, naphthyl,pyridyl, substituted phenyl where the substituted moiety is at least onemember of the group Consisting of CH3, C2H5, CHgO, CZH5O, "OCH2O', H0,F, Cl, Br, N0 NH and dialkyl amino containing 1-6 carbon atoms per alkylgroup.

2. A compound as defined by claim 1 wherein said compound is2,6-dichloro-3,5-dicyano-4-phenyl-pyridine.

3. A compound as defined by claim 1 wherein said compound is2,6-dichloro-3,5-dicyano-4-p-tolyl-pyridine.

4. A compound as defined by claim 1 wherein said compound is2,6-dichloro-3,S-dicyano-4-(p-ch1orophenyl)- pyridine.

5. A compound as defined by claim 1 wherein said compound is2,6-dichloro-3,5-dicyano-4-(m-nitrophenyl)- pyridine.

6. A compound as defined by claim 1 wherein said compound is2,6-dichloro-3,S-dicyano-4(p-nitrophenyl)- pyridine.

7. A compound as defined by claim 1 wherein said compound is2,6-dichloro 3,5 dicyano-4-(3-pyridyl)- pyridine.

8. A compound as defined by claim 1 wherein said compound is2,6-dichloro 3,5 dicyano-4-(4-pyridyl)- pyridine.

References Cited Lukes et al.: Chemical Abstracts, vol. 55, par. 1605-h;

January 1961.

HENRY R. JILES, Primary Examiner A. L. ROTMAN, Assistant Examiner U.S.Cl. X.R. 424-263

